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Everything at once
When major life events pile up
I was out in the wild making small talk with people I see semi-regularly, but don't know that well, and I made the mistake of asking the wrong person how his summer went, to which I got the following:
caution - sadness - caution - sadness - caution - sadness - caution - sadness
"Well, my dad died this spring, and then at about the same time I hit a deer with my truck going 95 miles an hour β it destroyed the front of my truck β[gave decent explanation for why he was going that fast] β then the first body shop I took it to did the worst job the second body shop I took it to has ever seen, but then after getting it fixed at the second body shop, it started making a whistling noise, and now they're trying to fix that. I haven't been to the lake much this summer because I can't tow my boat with the rental car, so that sucks. I've been trying to sell my dad's house and the [recent] inspection revealed all sorts of problems [varied in the boringness that is real estate, no offense intended to realtors or house inspectors] so I'm trying to get those worked out. [Indicates that this situation is up in the air]."
end - sadness

I have this guy's birth date but not the time. As he mentioned his dad's death, the inside of my head went "oh that's rightβhe had a Saturn transit to his sun this spring." Saturn won't kill all parents, but if Saturn or Pluto is headed for your sun and you have a living father, get him to that annual checkup ASAP (same goes for your mom if it's the moon). But you'll notice that's the only thing of finality in that story, though I assume the deer also died (sorry Bambi). Do you notice how everything else is up in the air? Not sure if/when he's gonna sell that house. That truck's been MIA for a while.
After walking a safe distance from everybody else, I loaded that chart, because of course I have my charts in my phone on the fly. And the transits are:
Sun β Saturn (as previously mentioned)
Neptune β Saturn
(possibly) Neptune β moon
Pluto β Venus
If you listen to people's stories while knowing astrology, interminable WTF-ness is a calling card for Neptune. With Saturn and Pluto, you know exactly TF, so when I hear malaise combined with a bad luck series of events, it's usually Neptune. Once when I had Neptune squaring some planets in my 8th house, my credit card number was stolen repeatedly: 3 times in (I believe) a 4 month span. The last time, it was somehow stolen despite the card remaining in its envelope and not-yet-activated (quote credit card customer service rep: "that shouldn't be possible"). It was a head-scratcher and, obviously, a headache. Anyway, the Neptune β Saturn transit is my most obvious culprit for the car/Bambi issue, though I suspect it may be a transit to the moon, as well. I would put money on the house selling when Pluto hits Venus again, and maybe he'll buy a new truck, since Pluto tends to do big-money stuff. Saturn's done with his sun, and Neptune's almost done with his Saturn, though it takes its sweet time wearing off.
Normally when it's a laundry list like the one given to me by this guy, it's multiple big transits at once, because life likes to do an everything-at-once type of thing to you, so I share it because it's a really good case study. How many people do you know who had some really crazy, unlikely stuff happen to them the week or month before or after a different big life event, like getting married, buying a house, or giving birth? Those major life events combined with additional craziness happen because they coincide with major planetary transits to your chart, and not all of them are friendly. The aforementioned credit card thing happened while I was divorcing, extremely broke, and had an additional cyclone of drama surrounding me at all times that I refuse to discuss ever again. Astrology makes it all make more sense, which is why it's interesting, and also why I use it. Not that you needed a reason...